This essay argues that Antony and Cleopatra questions both a binary vision of racialized sexuality and the colonial and imperial projects that such a binary legitimizes. Along with the seemingly whitest of men, Caesar, and the darkest of women, Cleopatra, this play includes a range of racialized sexual types. These include the virago Fulvia, the chaste wife Octavia, the eunuch Mardian, and the spectral figure of the “boy” catamite whom Antony, Cleopatra, and Caesar all fear becoming. These racialized sexual types converge in surprising ways in Antony and Cleopatra, and this convergence undermines any clear opposition between Roman virtus and its seductive and corrupting others. It also illuminates the contradictions and fissures within Roman ideals of self-mastery and self-determination that continue to shape modern ideals of respectability and responsibility. Antony and Cleopatra reveals empire to be a perverse enterprise indeed.